In a first foray into new territory, in 1992 the Pestana Hotel Group opens a hotel in Algarve, the first destination outside of Madeira and one of the group's core destinations, followed by hotels in Mozambique and Rio de Janeiro. In 1999, the group starts the expansion to Latin America.

The Pestana Hotel Group opens in 2001 the first luxury hotel, Pestana Palace Lisbon, member of The Leading Hotels of The World.In 2002, it reaches 5.000 rooms and 1.000 million on accumulated revenue. The group wins the concession of the Pousadas de Portugal by the Portuguese Government in 2003.

The Pestana Hotel Group reaches 10.000 rooms under its direct management. Towards new goals, in 2010, the group opened its first hotel in an european capital outside of Portugal, London, followed by hotels in Berlin and Barcelona. In the following year, across the Atlantic, the group opened another hotel in Miami, USA.